Hi, I'm new to the forums (but not to the site), and I was primarily interested in knowing what would be the ideal way to start automatizing my basic necessities.

My basic plan would be to:
-Have my credit card automatically get paid from my checking account at another bank.
-Wire my rent automatically transferred to the person who's room I'm renting.

I don't have to worry about utilities as it's included in my rent, but I want to know if there is anything that I should look at before implementing this.

Literally wiring your rent might be cost prohibitive. Most banks charge at least $20 for an outbound wire. But they will probably setup an ACH payment (like an electronic check) to your landlord.

I agree with automating most expenses, but manually reviewing my credit card is my last line of defense. So so many charges flow onto my card I prefer to review it every month and manually setup the payment. It is still electronic, but it is not automatically withdrawn from my checking account.

+1. Through years of trial and lots of error, I've learned that automating everything leads me to lose touch with my finances and things start getting out of control. I used to automate most things but now have gone back the other way and enter all my transactions manually (even though I have Quicken and could download them) and pay some of my bills manually.

The rule of thumb I use is this: if the bill is the same every month, I automate it; if it varies every month, I review it and pay it manually online.

I have recurring bills that are automatically paid from either my credit card or my checking account every month, such as telephone (I have a flat-rate package), internet, home alarm system, and a bunch of monthly charitable donations. For my credit card and cellphone bills, which vary each month, I review them first and pay them manually online.

Another thing I've learned the hard way: having bills paid automatically with your credit card is less desirable than having them paid automatically with your checking account, because credit cards are more vulnerable to being hijacked. It's happened to me three times in the past 10 years, most recently a couple of months ago, and it's a big hassle to have to update your credit card information with all of your service providers. Plus even if your credit card doesn't get hijacked it will always expire at some point, and you have to go through the hassle of updating the expiration date.

Checking account numbers don't expire, and it's more rare for ATM cards to get hijacked; this has happened to me too, but only once in the past decade, compared with three times for my credit card.